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$5,950,000
4 Beds ⋅ 4 Baths ⋅ 621338 MLS
Welcome to The Oasis on Ojibway! Introducing an extraordinary newly constructed waterfront estate that must be experienced in person. Perfectly positioned on a generous 13,200-square-foot double lot with 120 linear feet of waterfrontage, this one-of-a-kind residence showcases sweeping bay views, refined custom finishes, lush tropical landscaping, and effortless indoor-outdoor living. Designed with an inverted floor plan to maximize the panorama, the main living and entertaining spaces are located on the third floor, where walls of glass frame jaw-dropping views toward the world-famous Toilet Seat Cut. The spectacular gourmet chef's kitchen is equipped with Thermador appliances, a large center island, and a discreet hidden pantry. A private elevator services every level. The second floor hosts a family room and three bedrooms, including a serene primary suite, while the fourth bedroom is located on the third floor. Every bedroom captures breathtaking water views and offers access to the home's 2,400 square feet of balcony space. Outdoors, the property is equally impressive, featuring lush tropical landscaping, a private putting green, a beautiful swimming pool, and a charming gazebo--creating the perfect setting for entertaining family and friends. The concrete dock and cut-in boat slip have been fully reinforced and rebuilt, providing excellent accommodations for your boat and waterfront toys. Plans have also been approved by the Army Corps for a new 20,000-pound boat lift. Additional features include space for a trailer or RV and a 278-square-foot storage area. Situated on a quiet dead-end street beside a nature preserve, the home offers exceptional privacy within Islamorada's coveted Indian Waterways community, close to world-class fishing, waterfront dining, and boutique shopping. Owner/Agent. Call today!

195 Ojibway Ave, Tavernier

$5,900,000
13 Beds ⋅ 13 Baths ⋅ 621147 MLS
A rare and unique income producing Hotel in Marathon. Tropical Cottages is a boutique & profitable Mom and Pop Motel. Total of 11 valuable Transient Licenses, 13 Rooms plus office with kitchen & check in room. 9 buildings on the property, 8 adorable free standing cottages with new Victorian shingle roofs & the main building with 3 rooms in good condition. Each room has been tastefully and tropically renovated inside and out. Each room is unique & comes fully furnished. Most of the units have small kitchenettes including sink with microwave and refrigerator. All units have refrigerator & microwave. Additionally, there is a large Tiki Hut & Bar along with Food Truck with seating area. The Food Truck and Tiki Bar are leased for $6,375 per mos on a short term agreement. The Motel is managed by Owners . The hotel runs on auto-pilot. Online check-in available with a good housekeeping staff as back up. Most of the business is from repeat customers, plus online booking sites are all utilized. On site is a full laundry room with Commercial grade washers/dryers and storage rooms throughout. All housekeeping is done on site. Small, friendly & efficient staff has been there long term and willing to stay on with new owners. There are a total of 6 lots encompassing over 1/2 acre of land, total .56 Ac or 24,384 sf. Ample off street parking for guests. Zoning is GC and land use is recognized as Hotel/Motel. Bonus of Deeded waterfront access at the end of 61st St. which has a boat ramp and staging area for all types of watercrafts and sports. Same family ownership since 2010. Tropical Cottages was started back in the mid 1950's as a Fish camp and is one of the few remaining Mom & Pop Motels throughout the Florida Keys. Motel generates substantial Net income year after year to current owners. Sellers may consider Seller Financing may be available to a qualified buyer. Terms to be negotiated.

243 61st St, Marathon

$5,895,000
6 Beds ⋅ 6 Baths ⋅ 619297 MLS
This magnificent, exclusive estate on Duck Key offers a rare opportunity to own one of the most impressive waterfront properties in the Middle Keys. Set on a large, elevated, fully fenced and gated lot, the home boasts over 123 feet of protected deep-water dockage with approximately a 10-foot draft--ideal for serious boaters--along with sweeping, unobstructed views of Lake Lucille. Designed for both relaxation and entertaining, the outdoor space is truly resort-style. Enjoy a beautifully updated pool and spa, enhanced by new water features and a state-of-the-art outdoor sound system. The poolside cabana bar, complete with grill and a full-bath, creates the perfect setting for hosting guests in a private tropical oasis. Inside, the home is filled with natural light and elevated by soaring ceilings and elegant travertine marble floors. The spacious chef's kitchen is thoughtfully designed with seamless access to outdoor living areas, making indoor-outdoor entertaining effortless. The primary suite is conveniently located on the main level, while all guest bedrooms and bathrooms have been tastefully updated. Additional highlights include a rare wraparound balcony, a patio overlooking the pool and lake, a two-car garage, and an expansive basement offering exceptional storage. Boating enthusiasts will appreciate the multiple boat and jet ski lifts, as well as a floating dock. This is waterfront living at its finest--combining luxury, privacy, and unparalleled access to the open water.

152 N Indies Dr, Duck Key

$5,850,000
5 Beds ⋅ 4 Baths ⋅ 620179 MLS
Completely transformed down to the studs and scheduled for completion in late 2026, this extraordinary bay front estate represents the pinnacle of modern Florida Keys luxury. Meticulously rebuilt with elevated design, superior craftsmanship, and today's most coveted finishes, every detail has been thoughtfully curated to deliver an unparalleled waterfront lifestyle. Experience the ultimate Florida Keys lifestyle in this stunning bay front retreat in highly sought-after Tavernier. Perfectly positioned to capture endless turquoise water views and breathtaking sunsets. This exceptional residence features a raised metal roof, impact windows and doors, designer finishes, and sophisticated modern touches throughout. Designed for the boating enthusiast, the property features a private dock equipped with a 15,000-pound boat lift, providing effortless access to the Florida Bay and Atlantic Ocean. Enjoy a resort-style outdoor oasis with a pool, expansive waterfront entertaining areas, private dockage all overlooking the bay. Just minutes from Islamorada's renowned dining, marinas, sandbars, and offshore adventures. A rare opportunity to own a newly reimagined masterpiece in the heart of the Upper Keys.

233 Aberdeen Ct, Tavernier

$5,750,000
13 Beds ⋅ 7 Baths ⋅ 620213 MLS
Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe

$5,750,000
13 Beds ⋅ 7 Baths ⋅ 618705 MLS
Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe

$5,750,000
4 Beds ⋅ 5 Baths ⋅ 612702 MLS
Located in the prestigious gated community of Shark Key, 30 Cannon Royal Drive is a distinctive waterfront residence inspired by classic Mediterranean design. Architectural details such as soft arches, warm finishes, and elegant lines create a sense of timeless character rarely found in the Lower Keys. Thoughtfully designed to embrace indoor-outdoor living, the home offers spacious interiors filled with natural light and serene water views throughout. Two expansive porches overlook breathtaking sunset vistas, perfectly positioned on a generous 20,438 sq ft lot. The outdoor living experience is equally compelling, featuring a dedicated entertainment area complete with an outdoor fireplace and a private beach--ideal for both relaxed evenings and elevated gatherings. Additional highlights include two garages, an integrated indoor/outdoor speaker system throughout the home, and a dedicated space for a future elevator--offering both comfort and long-term flexibility. Whether enjoyed in its current form or reimagined to reflect a more modern vision, the property presents a rare opportunity to own a home with architectural presence and creative potential just minutes from Key West. Sold furnished with exclusions.

30 Cannon Royal Dr, Shark Key

$5,700,000
5 Beds ⋅ 5 Baths ⋅ 619762 MLS
TROPICAL ESTATE-Tucked away in the sought after exclusive neighborhood of Key Haven at mile marker 5. Spanning over half an acre this elevated, impact resistant, waterfront estate redefines island luxury. The private compound offers a stunning 3-bedroom 3.5-bath main residence alongside a beautiful 2-bedroom 1-bath bonus house, ideal for hosting extended family. For boating enthusiasts, the property boasts 2 docks-one private dock directly behind the home with gulf access, stunning sunset views and serene mangroves-the second is a deeded slip for a large vessel at the renowned Lunara Bay Marina, just across the street. Built in 2021 with impeccable attention to every detail, the main home showcases 10-foot vaulted ceilings, 9-foot doors, and an open concept design that seamlessly blends indoor and outdoor living. A wall of glass opens to a covered waterfront deck, creating the perfect sunset view for entertaining or relaxing in the coastal breeze. The gourmet kitchen featuring natural stone counter tops flows effortlessly into an inviting den, formal dining area and spacious family room with stone accent wall. Each space is thoughtfully designed with high-end finishes throughout. Step outside to your own tropical oasis, where lush landscaping features a rare collection of fruit trees including multiple mango varieties, key lime, lemon, starfruit, avocado and banana trees. Entire estate is equipped with automatic irrigation system and custom low voltage lighting. The resort-style pool is a true showstopper, complete with an infinity edge hot tub, water features, fire bowls, and dramatic pool lighting. Some additional highlights include a full-house generator, outdoor bar, security cameras, integrated sound system, elevator lift for accessibility and convenience, widow's walk and a private electric gate with dual entrances leading to a circular paver driveway.This is more than a home! This is a rare opportunity to own a True Tropical Waterfront Estate in Key West FL

29 Key Haven, Key Haven

$5,650,000
3 Beds ⋅ 4 Baths ⋅ 614935 MLS
Discover unparalleled privacy and tranquility in this one-of-a-kind oceanfront estate, a true sanctuary nestled amidst the untouched beauty of the Florida Keys. Tucked behind a private gate, the estate begins with a scenic drive through acres of pristine, preserved nature, leading to your own private island. This secluded haven, like no other in the Florida Keys, was once a source of inspiration for Budd Post—the visionary engineer behind the legendary Card Sound Road. It offers an extraordinary blend of history, natural beauty, and modern luxury. Surrounded by breathtaking 360-degree views, the property's expansive decks and waterfront tiki hut provide unmatched solitude and serenity. Here, you can reflect on days spent exploring the unspoiled waters of the Florida Keys, far removed from the bustle of everyday life. Crafted to perfection, the estate's concrete construction ensures strength and resilience while maintaining an air of timeless elegance. Inside, cathedral ceilings and a grand limestone fireplace create a warm and sophisticated ambiance. The dining room, framed by panoramic ocean views, offers an intimate setting for unforgettable gatherings. Three en-suite bedrooms promise unmatched comfort and privacy, making the home as functional as it is exquisite. This listing includes an additional lot offering even more possibilities and potential. Boasting over 200 feet of concrete dockage, and a private boat ramp, the estate is a boater's dream, offering the perfect gateway to explore the azure waters that surround you. Whether pursuing nautical adventures or savoring the peace of waterfront living, this property delivers an exceptional experience. This private haven is truly like no other in the Florida Keys—a rare gem where luxury, seclusion, and nature converge. Every corner of this secluded retreat invites you to embrace the unparalleled charm of coastal living in an enchanting and one-of-a-kind setting.

10987 County Road 905, Key Largo

$5,500,000
3 Beds ⋅ 3 Baths ⋅ 621388 MLS
Exceptional Investment Opportunity in the Lower Florida Keys! Owner and private financing are available. This is one of the very few vacation rental properties licensed for daily, weekly, or monthly rentals. Boasting an impressive occupancy rate and generating up to $400,000 annually, this property offers stress-free, passive income in Summerland Key, a premier location. Discover a rare gem in the heart of the Lower Keys! Recently remodeled to perfection, this luxurious three-bedroom beach house includes a sunroom with a palatial ocean view, currently used as a fourth bedroom. Just 20 miles from vibrant Key West, this coastal retreat features a private natural beach, breathtaking ocean views, and access to a private airport for island residents less than two blocks from the property. Don't miss this unparalleled investment opportunity!

481 E Shore Dr, Summerland

$5,500,000
6 Beds ⋅ 6 Baths ⋅ 618573 MLS
Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12' ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chef's dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views and the island's best spot to view the spectacular 4th of July firework show. Two charming detached guest cottages tucked amongst the gardens offer secluded retreats each with full baths and one offering a living room and kitchenette. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill; the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear Atlantic, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Don't miss the opportunity to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent. Seller is a licensed real estate broker and related to the listing agent.

906 Johnson St, Key West

$5,499,997
1 Beds ⋅ 2 Baths ⋅ 617777 MLS
This is a Rare opportunity to purchase a Turn-Key Highly Established Florida Keys Boat Rental Business and Marina located in the heart of Marathon Florida in Coco Plum and just minutes to Key Colony Beach. Opportunity includes a 15,500 sqft Deep Waterfront Lot that has quick unobstructed access to the Atlantic Ocean & Gulf of Mexico with Boat Dockage including 8 Slips, a well-maintained 5150 sqft Elevated Metal Building, which has just been newly painted and has 6 roll up doors including multiple that are 14 Ft High, a Fully Built Out Office Space with 1st Floor Bathroom & Laundry, a Paint Booth, Plenty of interior Storage for Boats, an Upstairs 1400 sqft Legal Dwelling, which has been Renovated and includes 1 Bed, 1 Full Bath, a Living Room & Kitchen & Impact Resistant Windows. Business is known for having one of most impressive Pristine Fleet of Rental Boats in the entire Keys including 18 Twin Engine Boats ranging in size from 25ft to 34FT in length including Many New engines. The maintenance schedule of the boats is impeccable with each Boat receiving Brand New Paint & New Upholstered Interiors with New Canvas on the T-Tops every few years, updated Electronics & they all received upgraded Twin Yamaha Motors over the last few years. There are 14 Aluminum Trailers for the Fleet, which are fully registered and road worthy. Total estimated values of all Business inventory including the Boat Fleet is almost $1.7M. You will not find any other comparable opportunity available in all of the Keys as this business has been successfully operated since 2007, has an estimated 80% of its business from repeat customers. So, if you have been looking for an opportunity to expand your Boat Rental or Marina business in the Florida Keys or if you have been dreaming about moving to the Florida Keys and owning your business, you may have just found the perfect opportunity as day 1 of ownership you are making money. Financials to be provided once NDA is fully executed.

91 Ave A Ave, Marathon

$5,499,000
6 Beds ⋅ 6 Baths ⋅ 621304 MLS
Experience exceptional waterfront living in this impressive Spanish-inspired concrete residence, built in 2019 and offering approximately 8,107 square feet of construction and 16,500 square feet lot size. Thoughtfully elevated and designed with an emphasis on space, quality, and comfort, this remarkable home showcases a highly customized interior with refined finishes throughout. Solid wood interior doors, generous room proportions, and carefully designed living spaces reflect the attention to detail found throughout the residence. Expansive recreational and entertainment areas on both the first and second floors provide exceptional flexibility for hosting, relaxing, and enjoying everyday family living. The home's substantial concrete construction and elevated design complement its commanding presence, while the spacious interior offers an ideal combination of elegance and functionality. Positioned along an exceptionally Deepwater, wide-canal home with direct ocean access, the property provides an impressive waterfront setting and a sense of privacy and tranquility. A distinctive luxury residence offering exceptional scale, generous entertainment spaces, and outstanding waterfront appeal. Ideally located near the airport and surrounded by a variety of restaurants, dining options, and everyday conveniences, the home offers an excellent balance of privacy, accessibility, and lifestyle.

108 Ave D, Marathon

$5,499,000
5 Beds ⋅ 5 Baths ⋅ 621212 MLS
At the very tip of a private peninsula in the heart of the Florida Keys, this stunning Gulffront property delivers the ultimate waterfront lifestyle. Built in 2022, this 4,146 sq. ft. Coastal Modern residence was crafted by one of Marathon's premier builders with meticulous attention to detail, blending clean architectural lines with the relaxed elegance of island living. From the moment you arrive, the Gulf is your constant backdrop. Expansive walls of glass flood the interiors with natural light and frame endless turquoise waters. Every living area, from the two spacious lounges to the gourmet kitchen, was designed to maximize the view and the connection to the outdoors. The chef's kitchen is both beautiful and functional, featuring waterfall-edge quartz counters, premium stainless appliances, and abundant prep space. Whether hosting a casual brunch or an elegant dinner, this open-concept space flows seamlessly to indoor and outdoor gathering areas. Five ensuite bedrooms provide private sanctuaries for family and guests. The primary suite is a haven unto itself, offering a sitting area, spa-inspired bath, and a private porch where morning coffee comes with dolphin sightings and golden sunrises. Step outside to a personal resort: a shimmering pool with sun shelf, expansive patios for lounging, and a palm-lined peninsula with a fire pit at its tip. A deep-water dock, private boat basin, and 4-post lift make boating effortless, with 5' control depth ensuring smooth access to open water. This home offers the convenience of an elevator, an oversized 2-car garage, and low-maintenance construction designed for coastal living. Located 5 minutes from Marathon Jet Center, you can go from tarmac to tiki torch in record time. Whether it's a weekend escape, seasonal retreat, or full-time residence, this Gulf Front estate offers something truly rare: privacy, luxury, and the beauty of the Keys wrapped into one extraordinary address. Fantastic Rental History. Offer Turnkey.

875 50th St, Marathon

$5,499,000
5 Beds ⋅ 5 Baths ⋅ 619946 MLS
Welcome to 142 Guilford Court, a stunning bayfront home located in the highly desirable and sought out neighborhood of Hammer Point. Built in 2021 with solid concrete construction and a concrete roof, this luxury waterfront home was designed for effortless Florida Keys living with panoramic bay views from both the the living spaces and primary bedroom, exceptional outdoor spaces, and high-end finishes throughout. Offered completely turnkey furnished and professionally decorated, this 5-bedroom, 5.5-bathroom residence features approximately 3,500 square feet of interior living space spread across three levels with elevator access to all floors. Every bedroom offers its own private en-suite bathroom, creating the perfect layout for hosting family and guests in comfort and privacy. The open-concept main living area is filled with natural light and framed by expansive impact glass doors overlooking the bay. The chef's kitchen includes premium appliances, quartz countertops, a large butler's closet/pantry, warming drawer, and generous entertaining space that flows seamlessly into indoor and outdoor living areas. Outside, enjoy a resort-style bayfront setting with a concrete dock, sparkling in-ground pool, multiple balconies and patios, fenced yard, covered parking, and breathtaking sunset views over the water. Whether you are looking for a full-time residence, luxury vacation home, or premier Florida Keys waterfront retreat, this property delivers the best of island living. Located in the Tavernier, minutes from Tavernier Creek and many dining venues, 142 Guilford Court is a rare opportunity to own a newer construction bayfront home in the Florida Keys with direct water access and timeless coastal design.

142 Guilford Ct, Tavernier

$5,400,000
6 Beds ⋅ 7 Baths ⋅ 621215 MLS
Step back into timeless Key West soul, where leaf-stamped garden paths, sun-dappled outdoor showers, and the gentle trickle of private pool waterfalls create an unforgettable Old Town sanctuary. Hidden behind a classic wooden gate just moments from the Historic Seaport and Duval Street, this compound offers two private, fully equipped homes on a lush 7,796-sq. ft lot, providing the ultimate luxury island retreat or multi-generational estate. Verdant foliage frames the wrap-around front porch of the front cottage, inviting you to sit back and enjoy quintessential island living. Inside, sky-lit vaulted ceilings with exposed wooden beams pour warm sunshine across white-painted walls and rich wood floors. The light-filled layout centers around an enchanting cottage kitchen filled with warmth and timeless charm that flows seamlessly into the living space and guest half bath. Three bedrooms-each featuring its own private ensuite bath-offer exceptional comfort. Floor-to-ceiling glass draws you out to an outdoor dining area and a sparkling heated pool nestled among vibrant gardens. Wander through the botanical grounds to the rear house, a custom-crafted two-story sanctuary built in 2016. Showcasing exquisite Hickory hardwood floors, whitewashed Cypress interior walls, and slate-tiled baths, this home balances coastal elegance with high-end luxury. The chef's kitchen boasts an elite ILVE range and custom cabinetry, flowing into open living quarters that slide open to the backyard oasis. The main floor offers versatile living with a guest suite that double-functions as a private home office with a built-in Murphy bed. Upstairs, a Craftsman staircase leads to a secondary guest suite with an ensuite bath and a sprawling primary retreat, complete with an oversized spa bath and a private balcony overlooking the second heated waterfall pool. Do not miss this rare chance to own one of Old Town's premier dual-home properties, complete with dedicated off-street parking for two cars.

613 Margaret St, Key West

$5,399,000
8 Beds ⋅ 8 Baths ⋅ 621248 MLS
Looking for a truly unique opportunity in the Florida Keys? Check out these 2 Custom Luxury CBS Pool Homes that are side by side! Live in one, and rent the other, corporate retreats, weddings, vacation rentals, tons of options! Experience luxury waterfront living in these custom-built, new construction two-story concrete homes featuring 4 bedrooms and 4 private en-suite baths. Designed for entertaining, the open-concept layouts seamlessly blends indoor and outdoor living. The chef's kitchens boasts top-of-the-line stainless steel appliances including double convection ovens, Smart refrigerator, dishwasher, vented range hood, prep sink, wine chiller, quartz countertops, custom cabinetry, and a large island. Porcelain tile flooring, custom fixtures, LED lighting, and abundant natural light enhance every space. A first-floor en-suite bedroom offers balcony access overlooking the pool, dock, and water. The dramatic floating staircase with custom LED chandelier leads to three additional en-suite bedrooms upstairs. The primary suite features a floating soaking tub, double vanity, custom porcelain tile shower, and MOEN programmable multi-head shower system with smartphone controls. Additional features include impact windows and doors, web-enabled security camera system, 4K Smart TVs in every room, 8-foot interior doors, two 3-ton 16 SEER A/C units, standing seam metal roof, aluminum railings, and expansive balconies on both levels. Located in the desirable Flamingo Island neighborhood of Marathon, just minutes from Sombrero Beach, dining, shopping, and entertainment. Enjoy quick access to open water, world-class fishing, boating, diving, and the crystal-clear turquoise waters of the Florida Keys. Built to impress and built to last, these exceptional waterfront retreats offer the ultimate Florida Keys lifestyle. Set up your preview today!

835 & 837 Copa D Oro, Marathon

$5,200,000
3 Beds ⋅ 3 Baths ⋅ 621314 MLS
Welcome to Your Private Oasis in the Heart of the Florida Keys! Discover this hidden gem, a secluded gated estate nestled amidst the stunning landscape of the Florida Keys. Located directly on the sparkling waters of the Atlantic Ocean with 120' of protected deep-water dockage on canal, this property is perfect for boating enthusiasts. This half-acre estate exudes charm and casual elegance, with wide, sweeping porches at both the front and back, providing the perfect setting for outdoor relaxation and entertaining. Inside, you'll find three spacious bedrooms, three luxurious baths, and a cozy den that offers versatile living space. Beautifully landscaped with mature tropical plants, this home features a stunning pool set amidst lush gardens, creating your own slice of paradise. Plus, you're just a short walk from the Millionaire FBO Jet Center, making travel to and from this exquisite location a breeze. Don't miss the opportunity to own this exceptional estate in the Florida Keys! Schedule your private showing today!

851 104th St, Marathon

$5,200,000
3 Baths ⋅ 617330 MLS
Prime Commercial Property in Iconic Key West - High Visibility & Versatility! This property offers a rare opportunity to own a substantial commercial footprint in one of Florida's most iconic destinations. Whether you're expanding a brand, launching a new concept, or investing in Key West's vibrant market, 3424 N Roosevelt Blvd is a strategic asset with flexible potential. Location Highlights include: • Strategic Location - Located on Key West's main commercial corridor • Proximity - 7 minutes (2.5 miles) to Key West International Airport • Exceptional Visibility - High traffic exposure from both locals and tourists • Surrounded by Amenities -Including hotels, restaurants, banks, shops, fitness centers, and grocery stores. Property Details • Building Square Footage: 3,420 sq ft • Building w/ Tiki: 7,491 sq ft • Lot Square Footage: 36,002 sq ft • Frontage: 155 feet Current Use • Vehicle - Rentals Currently operates as a successful vehicle rental business. • Service Department - Features a care center with six service bays. Business Opportunity sold separately, inquire with agent.

3424 N Roosevelt Blvd, Key West

$5,200,000
4 Beds ⋅ 4 Baths ⋅ 618184 MLS
Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound. Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT impact windows/doors, and Hardi board siding. Inside, enjoy a sunlit open-concept floor plan with soaring ceilings, a gourmet kitchen with quartz counters, premium stainless appliances, gas stove, a hidden butler's pantry, and a waterfront Bedroom wing, all oriented to frame the water from every room. Step outside and immerse yourself in resort-style living with a heated and chilled waterfront pool, soothing spa, hot tub, invigorating cold plunge, and a fire pit encircled by flickering tiki torches to gather with friends and family while sipping cocktails as the sun melts into the horizon. Lounge on the expansive covered porch while enjoying views of the peaceful nature preserve for incredible bird watching, and a setting that offers total privacy and serenity. Boaters will love the protected canal access with 2 boat lifts (8K & 12K lbs), just minutes from open water. Additional features include a 4-car garage with EV charger, covered RV Tiki with 50 amp service, whole-house 35kW generator (750-gal tank), whole house water softening system and Sonos throughout, including garage and outdoor zones. Whether you're seeking a private sanctuary, a trophy lot, or the ultimate Florida Keys lifestyle, Blue Sky Pointe delivers. This is the most premiere lot on Sugarloaf Key — a once-in-a-lifetime opportunity.

17013 Coral Dr, Sugarloaf

$5,100,000
5 Beds ⋅ 4 Baths ⋅ 621368 MLS
OWNER FINANCING AVAILABLE AT 6% Experience luxury waterfront living in the Florida Keys with this exceptional 5 bedroom, 4 bath estate, ideally positioned at the end of a quiet street with 173 feet of deep-water dockage and an expansive turning basin offering easy maneuverability for large boats, performance boats, and large sportfishing vessels. Offered fully furnished and completely move-in ready, this home is designed for effortless Keys living from day one. Furnishings, décor, and thoughtfully selected finishes complement the home's sophisticated design, while the chef's kitchen features a complete suite of premium Thermador appliances. Built for both luxury and durability, the smart home showcases high-end interior finishes and premium composite exterior materials designed for the coastal environment. Features include a private elevator, programmable smart-home hubs throughout, whole-house surround sound extending to the pool and rooftop, and two laundry rooms, one on each living level. Expansive indoor living areas transition seamlessly outdoors to a private resort-style pool with sun shelf and gazebo. Oversized balconies off the primary suite and kitchen overlook the water, capturing spectacular bay sunsets and views of boats passing through iconic Toilet Seat Cut. The nearly 2,000-square-foot rooftop terrace is a true showpiece, complete with turf, bar, BBQ area, immersive audio, and panoramic views. With direct bay access and a short ride to Tavernier Creek for convenient Atlantic Ocean access, this fully furnished waterfront estate delivers boating, entertaining, luxury, and the Florida Keys lifestyle in one extraordinary package.

265 Pueblo St, Tavernier

$4,999,999
5 Beds ⋅ 5 Baths ⋅ 621022 MLS
Looking for one of the most unique Bayfront Estates in the Florida keys, well you just found it. Just over 3 acres located on the Gulf of America. What makes the property so unique first and foremost is the privacy it offers. Upon entering the double gate, you are surrounded by huge trees, heavy foliage and vegetation which provides you with complete privacy. There are walking trails all through the entire property, including out to the Bayfront to enjoy some of the most spectacular year round sunsets you will ever see. The property directly to the North is a preserve called, Crane Point Hammock and Museum & Nature Trails. The subject property boasts its own huge boat basin with new custom Ipe wooden dock to accommodate large vessels and/or multiple vessels with two 50 AMP services, all the power you may need. There is a separate dock and slip tucked inside the private boat basin the owner had custom built for his 52 foot Viking Express. There is also a 20,000 pound boat lift and a small boat ramp for your flats skiff. The main home has that Old Florida Charm, three bedrooms, two baths and great room with exposed beams and tongue and groove ceilings. Take the stairs up you your private master retreat with spectacular views overlooking your private basin and the bay. The home also offers three screened lanais with water views. Attached to the main home is a private, separate entrance apartment with bedroom, bathroom and kitchen for complete privacy from the main living quarters. Across the pavered driveway is the detached three car garage and above offers a 1 bedroom, 1 bath, living room and kitchenette. The property is located 1.5 miles South of Marathon International Airport to make it easy for pilots and chartered jets and prop planes to come and go from this one of a kind Estate. Easy access to the Atlantic Ocean. Looking for peace, privacy and serene relaxing Florida Bay and sunsets views? You just found it!!

1590 Pelican, Marathon

$4,999,000
3 Beds ⋅ 3 Baths ⋅ 619743 MLS
A rare find with beautiful Atlantic ocean view, luxury oceanfront estate where architecture, nature, and experience converge into something truly extraordinary. Bali style modern villa with large outdoor entertainment area, perfectly manicured garden in the best neighborhood of Key Largo. Surrounding houses are in $7-8 million range. Buy the best priced property in the high end neighborhood. Set on an expansive 21,300 sq ft parcel with 86 feet of direct Atlantic frontage, this private sanctuary captures uninterrupted, cinematic views of endless turquoise waters - sunrises here are not just seen, they are felt. The residence embodies refined coastal modern living, where clean architectural lines meet the organic beauty of its surroundings. Every space is curated to frame the ocean, creating a seamless indoor-outdoor flow that elevates everyday living into a resort-level experience. At the heart of the property lies a spectacular 75-foot infinity-edge heated or chilled pool, visually merging with the Atlantic beyond - an illusion of swimming into the horizon itself. Complementing this is a private beach enclave and boat ramp, offering direct access to the ocean and the rare privilege of stepping into your own stretch of the Atlantic. This is more than a home - it is a personal retreat, an entertainer's dream, and a strategic oceanfront asset in one of Key Largo's most sought-after locations. Whether envisioned as a primary residence, luxury retreat, or investment opportunity, this property offers a lifestyle defined by privacy, prestige, and possibility.

60 Ocean Front Dr, Key Largo

$4,995,000
4 Beds ⋅ 5 Baths ⋅ 620618 MLS
Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

1616 Atlantic Blvd Unit 11, Key West

$4,975,000
5 Beds ⋅ 5 Baths ⋅ 619693 MLS
Experience elevated Florida Keys living at this exceptional waterfront estate in Buccaneer Point. Perfectly positioned on a prime oversized lot, this 5-bedroom, 5-bath residence offers the ultimate blend of luxury, privacy, and boating lifestyle. Designed for both entertaining and everyday comfort, the home features spacious open living areas, an elevator, and seamless indoor-outdoor flow to the resort-style pool and spa. Boaters will appreciate the impressive 225-foot dock, 25,000-lb boat lift, and quick access to world-class fishing, diving, and open water adventures. Multiple outdoor living spaces capture the beauty of the Keys, while the rooftop terrace delivers sweeping panoramic views and unforgettable sunsets. Whether you're seeking a full-time waterfront residence or a luxury island retreat, this property offers the rare combination of elegant living, exceptional dockage, and the laid-back sophistication that defines Key Largo.

112 N Bounty Ln, Key Largo

$4,950,000
1 Baths ⋅ 614960 MLS
Exceptional commercial waterfront opportunity in the heart of Marathon. This prime commercial property consists of five contiguous lots totaling approximately 30,000 square feet, with 300' on Coco Plum Dr and 300 feet of waterfront. The property includes 18 boat slips with a control depth of approximately 5 feet, offering outstanding maritime access and functionality. Zoned MU-M (Multi-Use Maritime), this versatile zoning allows for a broad range of uses including maritime industry operations such as fishing equipment sales and service, seafood processing, marine-related manufacturing, and boat storage. Additional permitted uses include retail, restaurant, affordable housing, and residential development, making this a uniquely flexible investment property. Parcel IDs include: 00362930, 00362940, 00362950, 00362960, and 00362970. The seller will provide a complete list of all personal property included in the sale, including major furniture, fixtures, and equipment. This is a rare opportunity to acquire a substantial, high-exposure commercial property with extensive waterfront and mixed-use potential in one of the most desirable areas of the Florida Keys.

38 Coco Plum Dr, Marathon

$4,950,000
4 Beds ⋅ 4 Baths ⋅ 618179 MLS
Discover a luxurious oceanfront haven on Duck Key, Florida, listed at $5,250,000. This 4-bed, 4-bath, 3,417 sq ft home on a 10,070 sq ft lot in Plantation Island blends elegance with island charm. Built in 1965 and exquisitely updated in 2019 with brand new AC, Electric and Plumbing. It features shell stone-wrapped walls, iceberg marble floors on the first level, and onyx marble upstairs, with a book-matched slab in the master suite. The gourmet kitchen boasts a La Cornue gas stove, ideal for hurricane season. Enjoy 72 ft of deep-water dockage with 20,000 lb and 10,000 lb boat lifts, coral stone steps to a canal, and access to a private Duck Key boat ramp ($10 fee) and marina for safe storage and fueling. Fish for tuna, mahi-mahi, and snapper near deep ocean drops and humps, with easy bayside access via nearby bridges. Lush mango, guava, and plantain trees, plus bougainvillea, create a tropical oasis. Duck Key, 60 miles from Key West and 100 miles from Miami, offers 230 sunny days, 70s-90s temps, and no state income tax. Join the optional Duck Key clubhouse for a pool, tennis, pickleball, and events, or Hawks Cay Resort for its Michelin-rated Salt and Ash restaurant, saltwater lagoon, Dolphin Connection, and pools. Relax at Grassy Key Sandbar or dive into vibrant marine life with dolphins and manatees. With top schools and a tight-knit community, this home, steps from the island's entrance, features calacatta stone, Restoration Hardware furniture, and marble baseboards. Cash, conventional, or seller financing available.

210 W Seaview Cir, Duck Key

$4,900,000
6 Beds ⋅ 5 Baths ⋅ 621334 MLS
Experience modern waterfront living at its finest in this exceptional Key Largo residence where striking contemporary design meets the effortless luxury of the Florida Keys. Built in 2023 and spanning 4,787 square feet, this 3-story home offers 6 bedrooms, 5 baths and spectacular water views from nearly every room. Designed for both entertaining and an everyday escape, walls of glass fill the home with natural light while connecting the sophisticated interiors to expansive outdoor living spaces. The resort-style infinity pool features a sun shelf, submerged bar seating and massage jets, all overlooking the water. A rooftop deck and upper terrace capture ocean views, while a covered summer kitchen creates the perfect setting for sunset dinners and entertaining. Boaters will appreciate 70 feet of concrete dockage, a 20,000 pound boat lift and deep-water access that puts the Atlantic in your backyard. Inside, the chef's kitchen and oversized island anchor the open living space, complemented by a dramatic climate-controlled glass wine display. A private theater, versatile game room or gym, and elevator connecting all three levels add another layer of comfort and sophistication. From mornings on the water and endless shades of blue to evenings with breathtaking sunsets, 64 Andros Road offers the ultimate Keys lifestyle: modern, private, sophisticated and designed for those who want to live as beautifully as they play.

64 S Andros Rd, Key Largo